Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 17, Problem 34P
On heating, cis-4-hydroxycyclohexanecarboxylic acid forms a lactone but trans-4-hydroxycyclohexanecarboxylic acid does not. Explain.
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Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.
When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone A.Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide B.Why doesn’t the cis isomer yield the oxide? C.Write the mechanism for each of the two reactions.
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Practice Problem 17.1 Give an IUPAC systematic...Ch. 17 - Prob. 2PPCh. 17 - PRACTICE PROBLEM
17.3 Which acid of each pair...Ch. 17 - Practice Problem 17.3 Write structural formulas...Ch. 17 - Practice Problem 17.4
Show how each of the...Ch. 17 - Practice Problem 17.5
Show how you could prepare...Ch. 17 - Practice Problem 17.6
(a) Which of the carboxylic...Ch. 17 - Prob. 8PPCh. 17 - Prob. 9PPCh. 17 - Practice Problem 17.9
Esters can also be...
Ch. 17 - Prob. 11PPCh. 17 - Prob. 12PPCh. 17 - Practice Problem 17.12
What products would you...Ch. 17 - Practice Problem 17.13 (a) Provide the reagents...Ch. 17 - Prob. 15PPCh. 17 - Practice Problem 17.15 Using decarboxylation...Ch. 17 - Practice Problem 17.16 Diacyl peroxides, ,...Ch. 17 - Prob. 18PCh. 17 - Give an IUPAC systematic or common name for each...Ch. 17 - Prob. 20PCh. 17 - Prob. 21PCh. 17 - 17.21 What major organic product would you expect...Ch. 17 - Prob. 23PCh. 17 - Prob. 24PCh. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - 17.26 What products would you expect to obtain...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - 17.28 Indicate reagents that would accomplish each...Ch. 17 - Write structural formulas for the major organic...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - 17.33 On heating,...Ch. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - 17.36 Show how pentanoic acid can be prepared from...Ch. 17 - 17.37 The active ingredient of the insect...Ch. 17 - Prob. 39PCh. 17 - Prob. 40PCh. 17 - Give stereochemical formulas for compounds AQ:...Ch. 17 - 17.41 -Glyceraldehyde can be transformed into...Ch. 17 - Prob. 43PCh. 17 - 17.44 Cantharidin is a powerful vesicant that can...Ch. 17 - Prob. 45PCh. 17 - 17.44 Given here are the NMR spectra and carbonyl...Ch. 17 - Compound X (C7H12O4) is insoluble in aqueous...Ch. 17 - 17.45 Compound Y dissolves slowly when warmed...Ch. 17 - Prob. 49PCh. 17 - Prob. 50PCh. 17 - 17.52 Starting with 1-naphthol, suggest an...Ch. 17 - Suggest a synthesis of ibuprofen (Section 5.11)...Ch. 17 - Prob. 53PCh. 17 - Prob. 54PCh. 17 - Prob. 1LGPCh. 17 - Prob. 2LGPCh. 17 - Prob. 3LGPCh. 17 - Prob. 4LGPCh. 17 - Prob. 1QCh. 17 - 17.2 Which of the following would yield...Ch. 17 - 17.3 Which reagent would serve as the basis for a...Ch. 17 - Prob. 4QCh. 17 - Complete the following synthesis.Ch. 17 - 17.6 Which of these acids would undergo...
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